3-(trimethylsilyloxy)estra-1,3,5(10)-trien-17-one | 1839-54-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-(trimethylsilyloxy)estra-1,3,5(10)-trien-17-one
• 英文别名: (8R,9S,13S,14S)-13-methyl-3-trimethylsilyloxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 1839-54-9
• 化学式: C₂₁H₃₀O₂Si
• 分子量: 342.554
• InChiKey: FRJOUBWXHQBBER-BNDYYXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methylenedimethyl sulfurane 、 3-(trimethylsilyloxy)estra-1,3,5(10)-trien-17-one 以26%的产率得到trimethyl(((8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxiran]-3-yl)oxy)silane
  参考文献：
  名称：

  Syntheses of selenoestrogens

  摘要：

  DOI：

  10.1021/jo00330a005
• 作为产物：
  描述：

  16β-Bromoestra-1,3,5(10)-triene-3,17β-diol 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 24.0h， 生成 3-(trimethylsilyloxy)estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Syntheses of selenoestrogens

  摘要：

  DOI：

  10.1021/jo00330a005

文献信息

• Einfache und stereoselektive synthese von α- und β-phenylglykosiden
  作者：Lutz-F Tietze、Poland Fischer、Hans-Joachim Guder

  DOI：10.1016/s0040-4039(00)85681-6

  日期：1982.1

  Reaction of phenyl-trimethylsilylethers (3) with 1-O-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucoside (1) (anomeric mixture) yields almost exclusively the aryl-β-glucosides (4) in the presence of catalytic amounts of TMS-triflate at 20°C, whereas (3) and 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-D-glucoside (2) gives mainly the aryl-α-glucosides (8).

  苯基三甲基甲硅烷基醚（3）与1-O-三甲基甲硅烷基-2,3,4,6-四-O-乙酰基-D-葡萄糖苷（端基混合物）的反应几乎只产生芳基-β-葡萄糖苷（4 ）在20°C下催化量的TMS-三氟甲磺酸盐存在下，而（3）和1-O-三甲基甲硅烷基-2,3,4,6-四-O-苄基-D-葡萄糖苷（2）主要产生芳基-α-葡萄糖苷（8）。
• The metabolism of 16-fluoroestradiols in vivo: Chemical strategies for restricting the oxidative biotransformations of an estrogen-receptor imaging agent
  作者：Anne C. Stalford、James L. Maggs、Thomas L. Gilchrist、B.Kevin Park

  DOI：10.1016/s0039-128x(97)00116-5

  日期：1997.12

  beta isomer was extensively glucuronylated at C(O)3 but also underwent aromatic hydroxylation and methoxylation before conjugation. Its C-17 epimer was subject to much greater aromatic hydroxylation but the catecholestrogen was O-methylated to a greater relative extent. The 16 beta-17 beta derivative underwent alicyclic as well as substantial aromatic hydroxylation and yielded numerous isomeric glucuronides

  16 α-氟-17 β-、16 α-氟-17 α- 和 16 β-氟-17 β-[6,7-3H] 雌二醇是由 [6,7-3H] 雌酮通过 3 的氟化制备的,17-双(叔丁基二甲基甲硅烷氧基)-[6,7-3H]雌三烯与 N-氟吡啶鎓三氟甲磺酸盐和 16 α/β-氟[6,7-3H]雌酮与 NaBH4 的还原。三种异构体通过硅胶相高效液相色谱分离。将它们静脉内给药（4 μmol/kg 给麻醉的雄性大鼠。它们的胆汁代谢物（6 小时内剂量的 90-97%）通过高效液相色谱-质谱法表征，并与 [6,7-3H] 17 β-雌二醇 四种雌激素及其羟基化和甲氧基化的代谢物以葡萄糖醛酸苷的形式排出体外。C-16 氟化阻止了 C-16 羟基化以及 C-17 羟基的脱氢。16 α-17 β 异构体在 C(O)3 处被广泛地葡糖醛酸化，但在结合前也经历了芳香族羟基化和甲氧基化。其 C-17 差向异构体发生更大的芳香羟基化，但儿茶酚雌激素的
• Highly atom economical uncatalysed and I2-catalysed silylation of phenols, alcohols and carbohydrates, using HMDS under solvent-free reaction conditions (SFRC)
  作者：Marjan Jereb

  DOI：10.1016/j.tet.2012.03.040

  日期：2012.5

  An uncatalysed silylation of phenols, regardless on the aggregate state and nature of the substituents with 0.55 equiv of HMDS under solvent-free reaction conditions (SFRC) at room temperature is reported. Sterically hindered phenols, carbohydrates and most of the alcohols additionally required a catalytic amount (up to 2 mol%) of iodine. The reaction protocol is very simple; obtaining a pure product, particularly of uncatalysed reactions, was frequently a completely solvent-free process. (C) 2012 Elsevier Ltd. All rights reserved.
• Reaction of trimethylsilylimidazole with 5,10β-epoxy-3-ketosteroids: Enolization and aromatization of the A-ring
  作者：S. Kulkarni、S. Abdel-Baky、P.W. Le Quesne、Paul Vouros

  DOI：10.1016/0039-128x(89)90150-5

  日期：1989.1

  The reaction of trimethylsilylimidazole (TSIM) and 3-keto-5,10-epoxy-nor-19-methylandrostanone 3 and its 17-acetate analog 4 was examined at two different temperatures. In both compounds, reaction at 90 degrees C gave predominantly a delta 3-silyl-enol ether plus a minor product as a result of the epoxide ring opening. Under reflux conditions, besides the aforementioned products, aromatization of the A-ring was observed as a major process. The results suggest the potential use of silylation reactions with epoxyketones towards the synthesis of aromatic compounds.
• KULKARNI, S.;ABDEL-BAKY, S.;LE, QUESNE P. W.;VOUROS, PAUL, STEROIDS, 53,(1989) N-2, C. 131-147
  作者：KULKARNI, S.、ABDEL-BAKY, S.、LE, QUESNE P. W.、VOUROS, PAUL

  DOI：——

  日期：——